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Thoughts about what work clothing always stays fashionable

April 10, 2019

When wondering what work clothing always stays fashionable, remember that some “fashion statements”, like Travolta’s pastel coloured jacket and trouser combo, fell flat!


Unlike Travolta’s Disco Suit, which died a natural death as soon as it was born in the 80s, some work-related products and services have survived – and thrived. So, what work clothing always stays fashionable? Read on to learn more.

Christian Dior evening ensemble, Zémire, H Line, AW, 1954.

Christian Dior evening ensemble, Zémire, H Line, AW, 1954.

About workwear and evening wear

There are some vintage workwear fashion trends, like Grunge – that of dull, drab, dirty, and hole-filled jeans and tees – that lived a short life. Others – like the Pencil Skirt, the crop top and jeans – have survived, and have evolved into becoming both formal office as well as evening wear classics.


The challenge for working women (and men too!) has always been finding that perfect balance between workwear and evening wear products. It used to be that designers in the past treated these as two separate fashion domains. However, modern designers, like Victoria Beckham and Stella McCartney have broken through those stereotypes, offering contemporary products and services in their line-ups that can be mixed and matched for both work and after-work use.


Our fashion editor has assembled a grand treat of what work clothing always stays fashionable. As you browse through this post, you’ll see a variety of ever-fashionable clothes – from the crop top and Tee, to formal evening wear and casual workwear. Inspiration for this piece has been drawn from a wide range of highly respected fashion sources, like The Lifestyle Network and Instyle, both of which are part of the Time Inc. network of companies.


For you to get a true sense of what work clothing always stays fashionable, our fashion editor and the entire team have worked hard to curate a selection of products and services and related ideas on this site, some of which we shall introduce in this post. Some work wear pieces discussed here, like the pencil skirt, have been around since Christian Dior’s “H-Line” collection came alive in 1954. Yet over time, they became cornerstone evening wear collections in many woman’s wardrobes.

Work clothing still fashionable

And the pencil skirt is an ideal example to understand what work clothing always stays fashionable. One would think that, since the 1950s is more than six-decades ago, work clothing from that era couldn’t still be fashionable – right? Wrong!

Yellow organdy gown by Dior publicity

Yellow organdy gown by Dior publicity


As our fashion editor points out, some products and services in the fashion arena seem timeless – and never tend to die out. They are so resilient, that they keep being reinvented and revived. While Dior may have dreamt-up the Pencil, contemporary fashionistas like Victoria Beckham have rejuvenated it into modern workwear must haves!


And talking about ever-fashionable work wear – what’s with a piece of clothing that’s been around since the 1870s? When talking about what work clothing always stays fashionable, we’ll be looking at that humble pair of jeans, that seems to continue to reinvent itself and blend into contemporary work and social fashion.


Our fashion editor and the entire editorial team have provided some helpful links embedded throughout this post. Clicking on the links to products discussed here will provide you even more information, and an opportunity to purchase some of those items.


We’ll also provide you with some amazing offers for products and services here. However, because we continue to refresh our site frequently to provide you with the latest opportunities, please note that some of these offers may be subject to change without notice.


So, if you wish to know what work clothing always stays fashionable, all you have to do is cast a look back at some iconic fashion pieces that are still in vogue today.

Woman wears cream two peice ensembl with pencil skirt, 1954

Woman wears cream two peice ensembl with pencil skirt, 1954

The Indispensable Pencil Skirt

There are any number of fashion products and services that have been designed and invented over the decades. However, when we talk about what work clothing always stays fashionable, a pencil skirt is probably one of the most indispensable pieces of work clothing in any woman’s wardrobe today. Like the famous crop top, which appeared in the late 1940s, pencil skirts have been part of the fashion scene since the 1950s. They’ve been standard workwear as well as part of a woman’s evening wear collection ever since.


From its early days, when Christian Dior created it as part of his New Look, the pencil has been an icon, both at the office and as evening wear classics. Marlene Dietrich wore it to fame in the Alfred Hitchcock movie Stage Fright in the 1950s. And then, we have Marilyn Monroe, who made the pencil famous with her iconic, form-fitting “wiggle walk”.


Fast forward to today, and as some of the links to products in this post will show, pencils are still going strong – though reinvented and revived for today’s work and evening wear tastes.

 Model wears vintage red satin blouse and tartan pencil skirt

Model wears vintage red satin blouse and tartan pencil skirt

Pencils Sharpened and Revived

To realise what work clothing always stays fashionable, look no further than celebrities like Michelle Obama, who frequently wore pencil skirts to Whitehouse working sessions, and also at after-work social events.


And while Britain’s very own Princess Meghan Markle has more recently re-invented her wardrobe “after Harry”, the power-pencil was the work clothing of choice for her paralegal character Rachel Zane in Suits.

Modern designers

More recently, modern designers like Victoria Beckham have introduced a contemporary twist into the timeless pencil skirt. Beckham’s Wool-blend midi skirt, available online at MyTheresa.Com, takes this wardrobe classic to new heights, making it as easy of an evening wear choice as it is a workwear pick. And if you’re wondering what work clothing always stays fashionable despite being introduced decades ago – here’s a thought:


The pencil silhouette of this particular Victoria Beckham piece ensures that it’s contemporary design still aligns with the vintage pencils from the 1950s. Anyone wearing this midi will feel they’re part of fashion history – but they won’t ever feel “historical”. Here’s why!

Radically different designs

Like so many of today’s popular products and services available in-store and online, including the crop top designs, modern pencil skirt designs are radically different from what we saw women wearing in the 1940s and 50s. Victoria Beckham has added a modern spin into her pencil design, which transports the wearer from the 1950s into the modern era.


The ribbed knit fabric, from which this midi skirt has been fashioned, is a viscose, polyamide and wool blend of Italian craftsmanship. And that makes Beckham’s signature masterpiece easy to blend into an evening wear ensemble, or it could be crafted into an office wear line-up using other existing pieces from your wardrobe.


If you are looking for work clothing to wear as an outfit primarily for the office, yet part of the time as casual wear, then you can comfortably pull off both looks with Beckham’s Wool-blend midi skirt.

Victoria Beckham in Düsseldorf, Germany, promoting her jeans range

Victoria Beckham in Düsseldorf, Germany, promoting her jeans range


For a formal office look, wear your Victoria Beckham midi with a tucked-in long-sleeved, collared, buttoned shirt. Either a plain white shirt, or a stripped version should do. Our fashion editor also has another recommendation that makes this midi an all-event pick.


For that evening wear look, substitute the shirt with a Poloneck Jumper available online at the Victoria Beckham International website. Alternately, you could choose a tonal sweater to go with the midi.

What work clothing always stays fashionable – Complete the look

In both cases, complete your office or evening wear look with over-the-knee leather boots of your choice. Since the pencil has historically been designed to go with heels, choosing boots with heels – even shorter ones – might be worth considering.


On a side note, if it’s an official (“work”) event that you need to attend – like an award ceremony or a retirement party for a colleague, then our fashion editor has a timeless, yet stunning, pick for you.


The black Curve Hem Fitted Dress from the Victoria Beckham collection is the perfect choice for dual-purpose wear. You could wear it to work in the morning, with flats for added mobility. Then, when it’s party-time, simply substitute your flats for a pair of black heels, and you’ve got the perfect evening wear for the occasion!

What work clothing always stays fashionable - Woman in jeans sawing a coffee table, c 1950s

Woman in jeans sawing a coffee table, c 1950s

Of Jeans and The Crop Top

When talking about what work clothing always stays fashionable, it’s unconscionable to speak about the timeless pencil skirt of yesteryear, and its modern evolution; yet omit discussing the crop top and jeans! Both of these are centrepieces of any woman’s work wardrobes, yet they can also be combined into evening wear.


Jeans – any style, any cut, and any design – are almost ubiquitous pieces of workwear ever invented. Who would have thought that when Levi Strauss and Jacob Davis created their first pair of jeans in 1873, it (the humble pair of jeans) would still be fashionable as work wear today! If you want an item of clothing to wear at the office part of the time, and yet have it available as evening wear at other times, then the ever-fashionable pair of jeans should work well for you.


The crop top too has remained fashionable work wear ever since it was created in the 1940s. While evening wear versions of this timeless garment might be worn with a cut higher above the midriff and belly, more “modest” office-appropriate designs are cut just above the waistline. This version of the crop top, combined with high-waisted jeans or dress trousers, makes for a perfect week-day ensemble to wear to the office.

What work clothing always stays fashionable - Woman wearing black crop top and mini skirt, 1989

Woman wearing black crop top and mini skirt, 1989

Combining Timeless Classics Together

While some of today’s fashion products and services will never really survive a single season – or at most a couple of years – others, like the crop top, jeans and the pencil skirt have been in vogue for decades. To blend these timeless classics into a good work wardrobe, you could take advice from the fashion editor at Real Simple and choose separates instead of traditional combos.


Rather than wearing a fitted pencil skirt and jacket, you could switch things a bit and try wearing your skirt with a V-neck top or sweater. That way, your outfit will double as an office ensemble as well as be perfect for evening wear.

So, what work clothing always stays fashionable if you are a crop top lover?

Well, this is yet another timeless classic that burst onto fashion fame in the 1940s, but came into its own during the 1970s and 80s pop revolution. So, how can something so “au-natural” from the Hippie movement blend into contemporary work or evening wear?


A crop top might ordinarily look like party wear. However, you could pull off a perfectly “respectable” office look if you wear it with a pair of appropriately-fitted dress pants – either wide-cut or tapered. If you work in a more “traditional” office setting, you could top that look with a long coat or a matching blazer – and you’ll still be wearing what is work clothing that always stays fashionable!


But don’t write-off your crop top as just something to wear for office use. You can easily prep it to be ready for evening wear in an instant. Wearing a crop top with a pair of well-fitted jeans and a long coat or jacket, makes for acceptable workwear in many offices and establishments today.


Optionally, pair your crop top with the Victoria Beckham Wool-blend midi skirt mentioned earlier could easily be pressed into service for a night out. Now, all you need is a light buttoned sweater or jacket, and you’re all set to paint the town!


If you aren’t particularly a “skirt person”, simply choose a pair of high-waisted bottoms – dress pants or jeans would do! A crop top with either jeans or trousers makes for ideal evening wear.

Pin-up photo of Anne Gwynne for US Army Weekly magazine Yank a weekly U.S. Army magazine in 1943

Pin-up photo of Anne Gwynne for US Army Weekly magazine Yank a weekly U.S. Army magazine in 1943

What work clothing always stays fashionable – Sourcing work clothing

Now that you know what work clothing always stays fashionable, you probably want to go out there and try sourcing an outfit that you can use for work and play. So, where might one go to get some of the products and services discussed here?


The best part of today’s fashion is that your work wardrobe can easily double for elegant evening wear too – AND, you don’t need to break the bank when doing so.

If you shop at Oxfam’s work-wear dress site online, you’ll find a few good links to products discussed here, as well as many other ideas for fashionable work-wear that never stops being fashionable.


Other great ways to find out what work clothing always stays fashionable, is to frequently go online and check out fashion thought-leading blogs and sites like Real Simple, Instyle, Lifestyle Group, Lifestyle Network, Food Collection and the Time Inc’s other related sites. In doing so, you’ll not only find great bargains on some of the products and services discussed here in this blog, but you’ll be exposed to a wide range of low-cost, evening wear and work clothing that always stays fashionable.

Disclaimers and Disclosures

All of the products and services displayed on this site have been especially curated for our visitors by a team of experienced professionals. Our fashion editor makes every effort to deliver only the most relevant and latest product offers to you. However, due to constantly evolving product manufacturer terms and conditions, some offers may be subject to change without notice. Please make sure you carefully review the Terms & Conditions section of each of the products and services you intend to purchase before placing an order.


Some of the links to products appearing here may have been sponsored by our partner advertisers and suppliers. This is done under formal agreement, between this website and manufacturers/suppliers, for compensation for some links. When making a purchase from our site therefore, it is important to keep in mind that we may receive compensation from some of the suppliers/retailers whose products are made available here.


Instyle and Real Simple are part of the Time Inc., The Food Collection and the Time Inc. Lifestyle Network. Real Simple is also a registered trademark of Time Inc.

All rights reserved. Copying, reproducing or distribution of our content without permission is strictly prohibited.


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